Bet on It
by HeatherTheMagnificent
Summary: Jack Frost makes a bet with his three friends, Pitch, Hiccup, and Jamie, that he's able to get the popular Rapunzel Corona to sleep with him
1. The Bet

_**Summary~ Jack Frost makes a bet with his three friends, Pitch, Hiccup, and Jamie, that he's able to get the popular Rapunzel Corona to sleep with him. **_

_**I just love Punk!Jack and Prep!Rapunzel c: **_

_**I've had this idea for awhile, and since I'm taking a break from Bare and Inked, I decided to write this one. **_

_**Disclaimer; I do not own Rise of the Guardians, How To Train Your Dragon, Brave or Tangled, (And for later a later chapter)Frozen. **_

_**The Bet**_

"Dude, don't tell me you're still hung up on Elsa?"

Jamie Bennett, one of Jack's best friends, said to him. They were sitting outside of the school and Jack was leaning against the wall, his eyes closed. He could hear Hiccup mumbling something about Elsa, but he honestly didn't care what.

He opened one eye so he could look at Jamie "I'm not." he closed his eye again and leaned his head back against the wall to continue his thinking.

Elsa Arendelle, or as Jack's friends would call her, the Ice Queen, was Jack's recent ex. Why did they call her the Ice Queen? Simple. She hated his friends. She thought they were "bad news" and hated him hanging out with them. It got to the point where she would get mad at him anytime he even mentioned their names, so, he left her.

"Man," Hiccup sat down next to Jack and put a hand on his shoulder causing Jack to open his eyes and look at him "move on."

It was no secret that they hated Elsa just as much as she hated them. Jack swore up and down that she was actually really nice, but it never showed when around them "What so you mean 'move on', Hic? It's been months. I think I'm fine."

"I think you're lying, bro." Jamie said sitting on the other side of Jack. He shot both Jamie and Hiccup both a look before shaking his head and running a hand through his hair "We need to get you someone new"

Jack smirked and chuckled "Oh, because you have such a great taste in girls."

Jamie pointed a finger at his face and mock glared "I won't hesitate to tell Astrid you said that."

Hiccup smiled "But on a serious note, Jack. You haven't dated anyone since Elsa. Which was last year, you have all these girls basically bowing at your feet. Just choose one!"

Jack shook his head again and stood up "I'm enjoying my life being single, guys. Let it go." Jamie started laughing and Jack glared down at him "What are you laughing at?"

"You!" Jamie stood up and got in front of Jack "You need someone in your life."

Jack raised his eyebrow "Why is that?"

"Senior year," Hiccup said, throwing an arm around Jack's neck "you're supposed to have fun!"

Jamie shrugged and chuckled "Or at least just get laid"

Jack smiled and looked away from them. If you wanted him to be honest, this wasn't the first time they've pressured him into trying to date someone. They've listed of plenty girls that would gladly date him, but he refused them all.

"Ana would date you."

"So would Merida. I think Astrid said she use to have a crush on you." Hiccup said with a shrug.

Jamie looked over at him, eyes wide "What?!"

Jack pushed the two away from him while they argued whether or not Astrid use to have a crush on him. He was going to go back to leaning on the wall when the last person to their 'group' came around the corner. "Hey Pitch"

"Jack," he then looked over at Hiccup and Jamie "Hiccup, Jamie. I have come up with a little... Bet for Jack here."

Jack rolled his eyes. Pitch's bets were never fun. One of them almost got Jamie expelled once. Pitch was standing there, hands behind his back, a smile on his face. Jack had chosen never to partake in any of the bets, but Pitch seemed to have made this one especially for him "We know how he's been down since Elsa started dating Hans."

"Wait, she's dating him?"

Pitch ignored him and continued talking "And I think it's time to set him up with someone using a bet."

Jack rolled his eyes and crossed his arms "I don't want to be set up with anyone."

"Shut it, Jack. You're doing this. You've never backed out of a dare so why back out of a bet?" Jamie said with a smile.

Jack sighed. Jamie was right, he couldn't name one time when he backed out of anything. He's been dared to do things he'd be embarrassed to admit. Once at some party they were playing truth or dare and Jamie thought it would be funny to dare Jack to make out with Hiccup. He hesitated, but did it anyways. "Okay, you got me. What is it?"

Pitch's smile widened. "Rapunzel Corona." Jack tilted his head to the side. He knew the name. Why couldn't he put a face to the name? "I bet you that you won't be able to sleep with her."

Jamie and Hiccup started laughing, both their hands on Jack's shoulder. Jack looked at the both of them, just waiting for them to calm down "Who's Rapunzel?"

Hiccup stood up straight and took a breath "One of the most popular girls in school. Flynn Rider's step sister?"

Jack thought about it before nodding "I think I know who you're talking about."

"You don't stand a chance with her, dude. She's hot!"

Jack glared at him before looking back at Pitch, who still had a smile on his face "Is it a bet?" he asked, holding a hand out.

Jack thought about it. He was able to make any girl fall for him within a matter of days if he really tried, so getting Rapunzel in bed shouldn't be so hard, right? He took Pitch's hand and shook it "It's a bet."


	2. Meeting Rapunzel

_**Meeting Rapunzel**_

Jack was standing near his locker, looking around for Rapunzel. He shook his head and laughed to himself when a thought hit him - he has no idea what Rapunzel looks like.

He he walked away from his locker and towards Hiccup's for a little help. Might as well start the bet while he still has the nerve. Hiccup was standing with Jamie and Astrid, Jack rolled his eyes and walked over "I have a question."

Astrid looked over at him and crossed her arms, glaring "Jamie told me about the bet. It's so wrong to mess with someone's feelings like that."

Jack just shrugged and put his arms around both Hiccup and Jamie "These two told me I needed to have some fun senior year, so why not?"

Astrid stepped away from Jamie and punched Jack in the arm multiple times "Jackson Overland, you are such an idiot for even wanting to play a girl like that!"

Jack took a few steps away from her so he was now standing behind Hiccup and rubbing his arm. Hiccup and Jamie on the other hand, were almost on the ground laughing from his face. Astrid then turned to Hiccup and punched his arm "That's for making him go along with it! And you, Jamie," she turned to face him "you know that she's one of my close friends, so why in the hell would you tell me about it and think I'm okay with it?!"

"Why didn't he get hit?" Hiccup asked, a hand on his arm.

Astrid shot him a glare "I'm dealing with him later."

Jack chuckled and stepped out from behind Hiccup "Now, the reason I actually came over to you guys, who exactly is Rapunzel?"

If looks could kill, Jack would be dead. Astrid was glaring daggers at him and her face was turning red with anger "Are you kidding me, Jackson?! You're going to sleep with her and you don't even know who she is?!"

Hiccup leaned over to him "She's got long blonde hair, green eyes, she usually will carry her shoes around instead of wearing them."

"She's kind of hard to miss. She's always either with Astrid, Merida or Ana." Jamie added.

"Obviously she's not _always_ with Astrid." Jack said pointing to her "She's with us"

Astrid reached forward and punched Jack in the arm again "I swear to God, Overland!"

Jack was smiling and shrugged "Listen, I'm going to go find her before Astrid makes my arm fall off"

Hiccup and Jamie nodded and watched Jack walk away. Hiccup chuckled and looked back at Astrid "I can't believe you had a crush on him"

"Shut up!" she shrieked before turning around and stomping towards her class.

**xxxxxxxxxxxxxxxxx**

Jack was back to looking around the hall for the girl with the long blond hair and possibly no shoes. He sighed in frustration and ran a hand through his hair before pulling his phone out to check the time. He only had a couple minutes until class started, which meant he had a couple of minutes to find Rapunzel.

He was about to give up and just go to his class when he saw blond out of the corner of his eyes. He mentally crossed his fingers hoping that it was her. He looked over and saw her standing with two other girls, a redhead, who he knew was Merida, and a shorter girl with black hair, who he guessed was Ana.

He smiled to himself when he caught sight of Rapunzel's face. He could tell right off the bat that she was innocent. Probably didn't do anything wrong. Any girl like that would love the chance to let loose a little.

He took a deep breath before walking over to the group of three. He gave Ana and Merida a smile before putting his attention on Rapunzel, who had yet to acknowledge him. He leaned on the locker next to her "Rapunzel, right?"

Rapunzel face him and looked him up and down before pulling another book out "Yes. And you're Jack Overland. What do you want?"

Sassy. He could deal with sassy. He gave her one of his charming smiles, getting a reaction from the other two "I'm interested in getting to know you."

He could hear Ana and Merida whispering behind him. Rapunzel stopped what she was doing and turned completely turned to face him "I'm not interested in getting to know you though. I know what kind of person you are."

Jack smirked and raised an eyebrow at her. "I've never met you before. How do you know what kind of person I am?"

"I've heard how things went with your ex."

"Rumors."

Rapunzel rolled her eyes and shut her locker. "Listen Jack, I'm not interested. But if you're so interested in me, ask your best friend. I dated him." she walked away before he could say anything, leaving him with Ana and Merida.

He watched her walk away before what she said clicked in his head "Wait, what?" He pushed himself off the locker and followed her "What do you mean you dated my best friend? Which one?"

Rapunzel laughed, but her face showed no sign of a smile "Hiccup. I'm surprised he didn't tell you since you two are so close."

"When did you date him?"

Rapunzel stopped walking and looked at him "It's really none of your concern when I dated him. I told you I wasn't interested, now will you please, go away?"

This tiny girl trying to act so tough. It actually made him laugh "I'm not a bad person, Rapunzel." she started walking again and Jack followed "So you have a past with my best friend, whatever. I'm not interested in that, but I am interested in you. Elsa and I ended on bad terms, and all you know about it are rumors. Get to know me, Rapunzel. I promise I'm not bad"

Rapunzel stared at him. He actually thought she was thinking about it. She stopped outside of her class and shook her head "Sorry, but I'm still not interested in getting to know you." she turned and walked into her class.

Jack was liking her personality so far. Sassy and feisty. He could deal with that. He turned to walk towards his class but a hand on his shoulder stopped him "What do you think you're doing talking to her?"

Jack smiled. He knew he was going to have to deal with Flynn at one point while getting to know Rapunzel, he just didn't know it was was so soon "Good to see you again, Flynn." he pushed Flynn's hand off of his shoulder "I'm being nice. Making friends. Rapunzel happens to be one that I would make friends with."

Flynn glared at him, not liking the sound of his sister hanging out with Jack. "You two are complete opposites. Why would you want to be friends with her?"

Jack shrugged "Opposites attract."

"You better watch what you do to her, Overland. If you so much as touch her, I'll hurt you."

Jack threw his hands up "Respect, dude."

Jack walked away before Flynn could say anything else. Dealing with Flynn was going to be fun, especially when he finally gets close to Rapunzel. He smiled to himself and shook his head.


	3. Opening Up

_**Friends or More?**_

It took a week to get Rapunzel to finally believe he wasn't that bad, and it was a long week. It consisted of meeting Rapunzel at her locker every morning, with Ana and Merida, who were already on his nerves. Astrid getting onto him and Flynn threatening him.

But after that long week, she was convinced.

Jack was relieved when she finally told him that she was willing to get to know him, that just meant one step closer to getting Rapunzel in bed.

"Do you have any plans today, Punz?"

Rapunzel smiled at him. She was letting her walls down and acting like herself, finally. He looked down at her when she was smiling, and he had to admit that she had a gorgeous smile.

"Nothing that I know of. Why?"

Jack smirked. He could use this as an advantage. Invite her over, sleep with her, end of the bet, he'd win. Then he started thinking of the bet, Pitch never did say what happened if he won or lost the bet. He did have a twisted mind, so who knew what he would make Jack do.

"Jack?" Jack was brought out of his thought by Rapunzel poking his side and saying his name "You just spaced out." she smiled before pulling her hand back to her "Why did you want to know?"

"Sorry," he started with a chuckle "I was wondering if you wanted to come over tonight? Watch some movies, introduce you to my sister, North, and Aster. Get to know you a little more." he shrugged "I wanna know what that real Rapunzel is like."

Rapunzel pulled her hair to the side and ran her fingers threw it "That sounds like it could be fun." she said with a smile "Actually, your sister sounds like fun. How old is she?"

"Fourteen."

Rapunzel jumped in her place and let out a squeal. Jack smiled at her. They had only been friends for a few days but it made him happy to see that excited over meeting his little sister.

Astrid walked over to them and grabbed Jack's arm, apologizing to Rapunzel and saying that she would return him in a few seconds "Jack, Pitch is getting impatient."

Jack stuck his hands in his hoodie pockets and smirked at her "I thought you weren't rooting for me"

Astrid glared and didn't hesitate in punching his arm "I'm not! But Jamie and Hiccup were too lazy to come over and tell you themselves. He wants to know whether or not it's going to happen so you can get your 'punishment' or whatever"

Jack's eyes widened "Woah, punishment?"

Astrid nodded crossed her arms "What was the bet for? What happens if you lose?"

"You know, Astird, I have no idea. Pitch never said." he shrugged and looked over his shoulder at Rapunzel who was talking to Ana "She's coming over tonight. Just tell him that" Astrid nodded and was getting ready to walk away but turned around and punched his arm again "What was that for?!"

"I'm still not happy about this!"

Jack rolled his eyes and walked back over to Rapunzel. She looked over at him with that same bright smile "What time should I come over?"

Ana's eyebrows raised and she looked between the two. Rapunzel? Going over to Jackson Overland's? She forgot that the two were even friends now. Just last week she was complaining about the guy.

"You can just come with me after school. It would be easier, I can take you home later."

Rapunzel nodded and grabbed her books she was going to need for the rest of the day, hooking her arm with Ana's and waving a goodbye to Jack "I'll see you later!"

**xxxxxxxxxxxxxxxxx**

Rapunzel met Jack at his locker that afternoon. She was going on about some kid, Snotlout, that was in her class and was always picking on her. Jack rolled his eyes. He knew Snotlout, obviously. He's Hiccup's cousin so he's been putting up with him since they met. **  
**

"You know the way to get to Snotlout? To get him to shut up?"

Rapunzel tilted her head to the side "How?"

"Just call him by his real name." he said shooting her a smile "Snotface."

Rapunzel started laughing and grabbed onto his arm to keep herself balanced so she didn't fall over from laughing so hard. "Are you kidding me?!" She said in between her laughing fit "Why in the world would someone name their child that?!"

Jack just shrugged and they started walking out to his car "Same reason Hiccup's name is Hiccup. It's a Viking thing. They are cousins, after all."

"They're cousins?!"

Jack chuckled and nodded "Yeah, how did you not know that?"

Jack opened the car door for her and she climbed in mumbling something about not knowing Hiccup's life like Jack does.

He glanced over at her once he got in "We have to pick Emma up." she nodded and pulled her feet up in the chair and leaning against the door "I guess I should warn you. Aster is my cousin, and can kind of be a jerk. Don't mind him though. North, is Russian."

"Russian? Isn't he your dad?"

Jack nodded "Technically. He adopted Emma and me." Rapunzel tilted her head and looked at him. She didn't know he was adopted. She had never met anyone else that had been adopted before "But he's Russian, loud, jolly, enjoys making toys. "

Rapunzel straightened up in her seat with a smile "Did you just describe Santa?"

Jack chuckled "I did." he looked over at her "He has the white beard and everything."

Rapunzel clapped her hands together "I'm excited to meet him!"

Silence took over the car. One thing was bothering Rapunzel, and she really wanted to ask Jack why him and his sister were adopted. But if he were anything like her, he didn't like talking about it. "Something on your mind, Punz?"

Rapunzel looked down at her hands and bit her lip. It was bothering her, she really wanted to know "If you don't mind me asking, why were you and Emma adopted?"

Jack took a deep breath and started drumming his fingers on the steering wheel. They had made it to the middle school and were waiting for in line for school to get out. Rapunzel almost immediately regretted asking him about it, and she was going to tell him he didn't have to answer but he started talking.

"I was eight at the time and Emma was four." his voice was soft. Rapunzel wasn't use to him being this cute, she was already use to him being loud "I really wanted to go out to eat on my birthday. I was eight, so going out to eat was a big deal for me. I liked food." he let out a laugh before he continued "On the way home, a deer ran in the middle of the road and my dad swerved, going off the road. My first thought was to protect my sister. My parents didn't make it, but we did. I was in the hospital for a while, but I'm here." he said holding his arms out and motioning to himself.

"If it makes you feel anymore, I'm adopted, too." she said, looking down at her hands again.

"Why?" he would love to change the subject off his parents. He was kind of shocked to hear that she was adopted though "If you don't mind."

"I lived with my mother, Gothel, for most my life. She would keep me locked up in the house, never letting me go outside. I never thought anything of it, really. I would do one wrong thing and... She'd hit me, or lock me up in a closet under the stairs for hours, sometimes I wouldn't even be allowed to eat for days." Jack hesitated before he reached over and took her hand to keep her calm "I met Flynn one day when I snuck out. I opened up to him, and he had promised not to tell anyone, but he told his parents. They called the cops, and they took my mother away."

"And then Flynn's family adopted you?"

Rapunzel nodded slowly "I was really upset with all of them for the first few months, but I love them. They _are_ my real family, I couldn't ask for better." She gave him a smile before letting his hand go to wipe her face "I'm sorry for just crying like that. I've never been able to tell anyone that before, they know I'm adopted, they just don't know why."

"I'm glad you opened up, Punz."

She gave him a shy smile before looking away. She didn't know what she was supposed to say to that. You're welcome? Me too? She looked out the window and saw a girl that looked like Jack walking towards the car.

Emma looked at Rapunzel, a little confused as she pulled open the back door and climbing in. Jack gave her a smile in the rear view mirror but before he could say anything Emma was glaring at him "Why is there a girl in the car?"


	4. First Kiss

_**First Kiss**_

"The girl has a name, Ems." Jack said as he started driving away from the school "And it's Rapunzel."

Emma leaned forward and studied Rapunzel's face. She was giving Emma a shy smile and then gave her a little wave. Emma smiled. Jack always told her to trust someone by the look in their eyes, and Emma didn't see anything wrong with her "Jack hasn't brought a girl home in months."

Rapunzel let out a sigh of relief. At least Emma was making conversation with her "Why not?"

Emma smirked. Rapunzel looked between the siblings. Their smirk was exactly the same, it kind of scared her a little "No one finds him attractive, that's why. And he's a jerk."

"Oh, haha, you're so funny." Jack said rolling his eyes "Don't corrupt Punz."

Rapunzel giggled and shook her head "She's not going to corrupt me."

Jack just shrugged and Emma leaned forward again, smiling at Rapunzel "Has he told you about our family?" Rapunzel nodded "How him and Aster get in arguments over small things, it's really dumb actually. Oh! And North and his cookies!"

Rapunzel smiled "He really does sound like Santa." she looked down at her hands and shrugged "The only people at my house are my parents and Flynn. Oh! And my pet chameleon!"

"Pet chameleon?" Emma and Jack asked at the same time.

Rapunzel nodded, obviously proud "He's been with me for as long as I can remember. His name is Pascal."

"A pet chameleon." Jack said again with a smile "That's awesome, Punz."

"We have a pet rabbit. Well, it's actually Jack's and he hates it."

"How could you hate a rabbit?" Rapunzel asked, shock written all over her face "They're so cute!"

"Not Bunnymund." Jack mumbled.

"Bunnymund?"

"He's named after Aster." Emma said with a smile and grabbed her bag as she got out of the car "You'll see why"

Rapunzel laughed and stared at the house. From the way Emma and Jack talked about Aster, it made her nervous to meet him. She slowly opened the door and slung her bag over her shoulder "Is Aster really that bad?"

Jack didn't even think before answering "Yes" He didn't realize he was making her nervous about it until right now "But don't worry, there's also the possibility that he's not home."

Rapunzel let out a sigh of relief. She felt a bit better knowing that she might not have to meet the guy that Jack doesn't get along with. She's been seeing this sweet side of him, she didn't want to have that all change just by some words.

Jack gave her a smile as she opened the door for her. She could hear Emma talking to someone in the other room and she sounded excited. Jack chuckled and walked towards where the talking was "Ems, chill. North has to hear this every day." he said as he picked up a cookie off the plate that was on the counter. He turned and offered one to Rapunzel who smiled and gladly took it "Let him talk to Punz."

North raised his eyebrows and turned to look at the girl standing in the doorway who was looking around the kitchen nervously. She waved, a small smile on her face "Hi, I'm Rapunzel"

"Ah! Rapunzel!" North said with a smile as he walked over to her, his arms, ready to pull her in for a hug "Jack has told us about you! Aster is wanting to meet the girl that is, and I quote 'wanting to spend time with an anklebiter like Jack'."

Rapunzel laughed as North let her go. She gave him a shrug and looked around him at Jack who was leaning on the counter "I'm more nervous to meet him. Jack and Emma both said he could be... Mean?"

North chuckled and put a hand on her shoulder "He's just like that towards Jack.

Jack made a noise behind him as Emma walked back into the kitchen carrying a grey rabbit "This is Bunnymund!"

Rapunzel smiled and reached out for the rabbit "He's so cute! Why don't you like him?"

"He's a jerk." Emma and Jack said at the same time.

As if to prove their point, Bunnymund went to bite Emma's hand. She shrieked and dropped the rabbit, causing Rapunzel to gasp and bend down, picking it up "You poor thing!"

Jack and Emma both watched as Bunnymund just settled into Rapunzel's arms. Jack glared at the rabbit "That isn't fair."

Emma reached for Bunnymund and started mumbling about how much of a jerk the rabbit was. Jack reached out and took a hold of Rapunzel's wrist "We'll be upstairs!"

Rapunzel was going on about how sweet of a rabbit Bunnymund was and that she hoped Aster was that nice. Jack rolled his eyes and shut his bedroom door. Rapunzel was walking around his room and looked at some of the stuff he had in there. Trophies, posters, pictures. she didn't realize that he ever did anything to get trophies.

She picked up a picture that was on his desk and stared at it for a few minutes. It was a picture of a younger version of Jack and Emma, and two people she didn't recognize, she figured they were his parents. She smiled and set the picture back down, turning around to face him.

She blushed when she realized he was in the middle of changing his shirt. She bit her lip as she looked him over. Not only did he have tattoos on his arms, but he had a few on his chest. She quickly looked away when he glanced over at her.

He smirked as he pulled his new shirt on and then told her to come and sit down. She kept her gaze anywhere but on him until he started talking "So, you liked the view, huh?" he asked her leaning back.

Rapunzel's face turned red and she shook her head "N-No! I-I mean, I'm not saying that I _didn't _like it, but I'm not saying that I did"

Jack smiled and reached over, running a hand down her arm, causing her to look over at him. Without hesitation, Jack leaned closer to her, waiting for her to tell him no or push him away. When he didn't get any protest he closed the distance between them and catching her lips in his.


	5. Elsa

_**Elsa**_

"Haddock!"

Hiccup turned away from his locker to see who was calling him. His smile immediately turned into a frown "What could I have possibly done to get the Ice Queen after me?"

Elsa rolled her eyes and stopped in front of him, crossing her arms "Who's Rapunzel?"

Hiccup raised his eyebrows "Why do you wanna know?" Elsa made a noise and glared at him "Are you planning on hurting her?"

"Why would I hurt her?" She uncrossed her arms and let out a frustrated sigh "I'm not going to hurt her, Haddock, I just need to talk to her. Who is she?"

Hiccup turned back towards his locker, getting the last of his books out before shutting it "Ask Anna. She knows everyone."

"Anna doesn't know I'm trying to find her. And I know she's Jack's latest girl, so I know you know who she is. So tell me"

"I'm not telling you."

Elsa grabbed his arm and turned him to look at her "At least tell me where Jack is"

Hiccup thought about it before shaking his head "I wouldn't send his ex girlfriend to him to ruin his relationship"

Elsa had never felt so irritated with Hiccup before. She knew he wasn't telling her just because he hated her. She groaned and let go of his arm "You're no help"

She turned and walked away from him, heading towards her sisters locker. She would rather just ask Anna who Rapunzel was instead of having to search for Jamie to get it out of him. She stopped walking when she saw that familiar white hair that belongs to Jack Overland.

He was leaning on a locker next to a girl who she assumed was Rapunzel. She took in Rapunzel's appearance. The blond hair that was tied up with a ribbon, the floral dress she was wearing, and she even had a cheer bag over her shoulder. A cheerleader with Jack Overland? Elsa let out a laugh, now she knew what Anna had told her was true.

The Jack Overland she knew would never go for a cheerleader.

She took one last glance at Rapunzel to memorize her face. She de died at lunch she was going to track her down and talk to her.

**xxxxxxxxxxxxxxxxx**

"Elsa? Who are you looking for?" Anna asked, taking a bite of her food.

Elsa looked over at Anna before shaking her head "No one. I'm just looking around."

Elsa turned her attention back to looking around the cafeteria. She couldn't find Rapunzel anywhere. She found Jack, sitting with Hiccup, Jamie and Pitch, but Rapunzel wasn't there. She looked towards the doors of the cafeteria when they opened and Rapunzel walked in with three of her friends.

One of them walked away towards the table that Jack was at but the other two stayed with her. Elsa stood up, telling Anna she'd be back and made her way towards Rapunzel.

"You're Rapunzel, right?"

Rapunzel turned away from her friends and gave Elsa a smile, but the confusion was written all over her face "I am. And you are...?"

Elsa glanced at her friends before motioning towards the hall "I need to talk to you."

Rapunzel hesitated before nodding and following her out into the hall "If you don't mind me asking again, who are you?"

"Elsa." she watched Rapunzel's face turn to confusion "Jackson Overland is bad news."

Rapunzel stared at Elsa. Why was she warning her about Jack? Why was his ex even talking to her? "Besides that you dated him, what makes you say that?"

"I don't know if you've met his friend Pitch or not, but my sister told me that she heard him talking to Jamie about some bet"

"What do I have to do with a bet?"

"That bet was to see if Jack could get you to sleep with him."

Rapunzel laughed and shook her head "Jack's been nothing but good to me. I'll admit that when he started talking to me that's what he wanted, but I've been to his house plenty of times before and he hasn't tried anything." she shrugged and adjusted her bag on her shoulder "Your sister could have heard wrong."

Elsa studied Rapunzel's face. This poor girl was falling for everything Jack was saying to her "I'm just warning you because you seem like a sweet girl. Jack really is bad news, just be careful when you're with him."

Before Rapunzel could say anything else, Elsa had walked off. Rapunzel shook her head, if anything, she was only thinking that Elsa could have made it up from jealousy.

* * *

"So, I met Elsa today."

Jack raised his eyebrows at her. He hadn't been expecting Elsa and Rapunzel to ever meet, that's weird for him "Oh yeah? How did that go?"

Rapunzel shrugged and looked up at him "If you want me to be honest, it was a little awkward. She was trying to tell me that you're bad news."

"Of course she was." he mumbled "What did she say?"

"Something about a bet."

Jack tensed up. Elsa knew about the bet? And she told Rapunzel? Jack stared down at Rapunzel. He was pretty sure she didn't believe it, but he could never tell with Rapunzel "A bet?"

Rapunzel nodded "It was really dumb. Personally, I think she may have made it up."

Jack let out a sigh of relief "That sounds like Elsa." Jack looked over his shoulder towards the direction of Anna and Elsa's locker "Hey, I'll see you later tonight though, okay? I have to talk to Hiccup." She nodded and he pulled her to him for a hug and pecked her lips before walking off.

Jack was trying to remember where exactly Elsa's locker was, but he couldn't. It had been awhile since he had been to her locker. He spotted Anna and walked over to her "Hey Anna, where's your sister at?"

Anna stared up at Jack with surprise "She could be at her locker... Why?"

"I just need to talk to her. Where's her locker at?"

Anna pointed down the hall "It's just down there"

Jack gave her a nod before he walked off and she watched him go. Him and Elsa had completely avoided each other since they had broken up, and now he was wanting to talk to her again? She wasn't sure if she was okay with it.

Jack finally found Elsa at her locker. He wasn't sure what he was wanting to say to her but he knew he wasn't happy with her telling Rapunzel. He walked over to her and leaned on the locker next to her "Long time no see, Elsa."

Elsa jumped, startled by Jack. She didn't even hear him walk up to her "Jack! What do you want?"

Jack smirked and looked at her "Rapunzel told me you talked to her." Elsa rolled her eyes, she knew Rapunzel was going to tell him, why did she think she wasn't? Elsa turned completely so she was now facing him "Why did you tell her? Did you think it was going to stop the relationship?"

"_That's_ not a relationship, Jack. That's just using someone to prove a point, and it's wrong. That girl is so innocent"

Jack shrugged and pushed himself off the locker "I know she's innocent. I also know what I got myself into, and it's really none of your business, but I actually care about her."

Elsa crossed her arms and glared at him "That's something I thought I'd never heard you say, Overland."

"Rapunzel's going to be around for a while, don't try to ruin it again. She's convinced your just jealous." he said with a chuckle and started walking away.

Elsa' se yes widened and she turned around to look at him "You know that's not true!"

Jack looked over his shoulder and smiled "I'm just going to let her think what she wants."


	6. Guilt

_**Guilt**_

Rapunzel stood in front of the mirror in her room, taking in her appearance. Jack was taking her out for their first date, and she didn't want to look _too_ preppy, but going through her clothes she found that she couldn't help it. All she owned was preppy clothes!

She stuck with a dress, the top was red and the bottom was black. She smiled to herself, it wasn't too bad.

She wasn't able to keep her excitement down. Sure, she had been on many dates before, but there was something about Jack that stood out to her. He was nicer to her than most guys were. He may be a punk, but he's got himself a sweet side.

She then let her mind wander to what Elsa had told her. That bet. Was Jack really just trying to sleep with her? She bit her lip and pulled her hair to the side, running her fingers through it. Jack didn't seem like that type of person. She tried to think of a time when it seemed like he was just using her, but she couldn't.

She figured if he was, he would have tried something by now.

There was a knock at her door and she looked over her shoulder to see Flynn "Hey brother" she said giving him a smile.

"You're going on that date with Jack, right?" Rapunzel nodded and he made a face at what she was wearing "Don't you think you should... Cover up more?" he asked motioning towards her outfit.

She turned back towards the mirror and tilted her head "I thought it looked okay"

"You look fine." he answered quickly, walking more into her room and looking around before throwing a sweater at her "But he's a guy, he'll be tempted because you're in a dress"

Rapunzel rolled her eyes but pulled the sweater on anyways "You're overprotective."

Flynn chuckled but nodded "I know. And don't forget, when you get home we probably won't be here."

Rapunzel nodded and pushed out the door so they could leave her room "I know, I know." there was a knock at the door and Rapunzel smiled, pushing past Flynn to get downstairs. She pulled the door open and then turned back around, calling up to Flynn "Tell them I'll come see them soon and that I love them!"

"Who do you love?" Jack asked raising an eyebrow.

"My grandparents."

Jack nodded and motioned towards his car "Shall we?" he held his other hand out for her to take.

"We shall." She said with a laugh, taking his hand.

They were only in the car for a few minutes when she turned to him with a smile, her hands clapped together "So! Where are we going?"

"Now Punz, that'll ruin the surprise."

Rapunzel pouted and leaned against the door.

Jack didn't seem like the romantic type. But he seemed to have something really special planned, and he seemed pretty excited. She was racking her brain tying to figure out what he had planned. She didn't know what he liked to do, if he liked taking his dates to the movies, or whatever it is he likes to do.

Jack reached over, taking her hand to calm her. He could tell she was nervous just by glancing at her.

"You'll have fun, I promise."

Rapunzel nodded and looked forward, still trying to figure out where he was taking her.

**xxxxxxxxxxxxxxxxxxx**

Jack figured that he should have at least introduced Aster to Rapunzel first before bringing her here, the thought never crossed his mind.

"The Warren?"

Jack nodded and got out to open her door for her "The Warren is a place owned by my cousin. It's a restaurant"

"Aster owns a restaurant?"

Jack nodded again "You'll finally get to meet him."

"That's an exciting date." she said with a laugh.

Jack chuckled and opened the door to The Warren for her. She walked in and looked around, the place was set up nice. How did she not know it existed? Once she was inside the smell of food hit her, and she couldn't deny that it smelled really good.

Someone walked over to them, glaring at Jack and giving Rapunzel a smile. "You must be Rapunzel"

She was a little taken aback by the Australian accent, but she smiled and held a hand out to him "And you must be Aster."

He took her hand with a smile "So he's talked about me?" Rapunzel laughed and nodded "I just have one question before getting you two a table" Jack groaned, knowing what was coming and Rapunzel tilted her head, waiting "What's a sheila like you doing with him?"

Jack put a hand on the small of her back and pushed her towards the tables "She's not going to answer that, you kangaroo. Just give us a table"

Aster's glare towards Jack hardened "Don't push it" Jack rolled his eyes and let Aster lead the way, pulling the chair out for Rapunzel. When Jack wasn't looking, Aster leaned down to Rapunzel "If he gives you any problems, just smack him."

Rapunzel laughed but nodded before she picked up the menu. Her eyes were scanning it over when Jack started talking to her "If you want me to be honest, I had no idea what to do for tonight." he reached over and took the menu out of her hands "But I asked Aster to help out and he said he'd make a special meal since I found a good girl."

Rapunzel smiled and picked up the water that Aster had brought them "What's the meal?"

Jack leaned back in his seat, a smile on his face "Again with ruining the surprises, Punz?"

She started questioning him about the meal. If it was something she liked, or something he liked, maybe something they both liked, if it was something she was allergic to. He stopped to think on that one, not really sure of the answer, but he hoped she wasn't.

Spaghetti. That was the special meal that Jack was keeping a secret from her, and ice cream for dessert, not that she was complaining about it.

"What else do you have in store?"

Rapunzel grabbed his hand as they walked out to the car. He looked up at the sky, staring at the moon before shrugging "I really only had dinner planned. I was just going to take you back to my house for movies or something."

"I like that idea."

Jack started the car and started towards his house. A thought hit Rapunzel and she reached over, placing her hand on his arm "Actually, if you want more privacy, my parents and Flynn shouldn't be home, so we can go to my house"

Jack smirked. She was making this too easy. He nodded and made a turn, heading towards her house instead.

She wasn't sure why she told him that. They'd be alone in her house, the first official time they'd be alone together for hours. She instantly got nervous, but covered it up with a smile.

They walked into the house, Rapunzel shutting the door behind them. She pushed him towards the stairs and led him to her room. He looked around and smiled, walking towards Pascal's cage "Where is he?"

Rapunzel frowned when she saw that Pascal had escaped his cage again "He really hates his cage." she looked around her room before her eyes landed on something and she walked over to her bookshelf, picking him up "Meet Pascal!"

Jack stood up straight and looked at Pascal. He was either going crazy, or the thing was glaring at him. Rapunzel walked by him and put Pascal away, mumbling something about staying in his cage. She turned and faced Jack "Well, this is my room" she said with an awkward laugh.

"It suits you."

He was standing in the middle of the room, still looking around when Rapunzel walked over to stand by him "I'm glad we went out tonight"

He smiled down at her and slipped an arm around her waist "I am too. We'll have to do it more often"

She nodded her head and Jack pulled her closer before leaning down and catching her lips.

It was slow at first, a pace Rapunzel happened to enjoy. Only when Jack took a step, pushing her towards the bed, did she make a noise, causing him to deepen the kiss. The two fell onto the bed, Jack tearing his lips away from hers to move to her neck.

He let his hands start to wander. She didn't seem to care, she was griping his shoulders with her head tilted to the side. His hand was under her dress, running up her thigh when she gasped and pushed him away "Jack!"

He sat up and ran a hand through his hair "Sorry Punz."

She shook her head, propping herself up on her elbows "Don't apologize. I... I want to. It's just I've never... You know?"

Jack kissed her cheek "We don't have to, Punz. I don't want to hurt you."

"I want to, Jack." she sat herself up completely so she was now level with Jack, her hands on both sides of his face "I trust you."

Jack felt a pain in his chest at the words. She trusted him, and he was just sleeping with her for some bet. He stared at her for a few seconds before nodding, there was no doubt in his mind that he actually felt something for her.


	7. Fall For You

_**Fall For You**_

"Being my longest and closest friend, you can't tell anyone, not even Jamie or Pitch, what I'm about to tell you." Jack said, pointing at Hiccup and propping his feet up on Hiccup's desk.

Hiccup raised his eyebrows and looked up from his textbook and over at Jack "Is it bad? Because if it's involving the risk of your health I'm at least telling Jamie"

Jack rolled his eyes and threw a pencil at him "No, it's not bad. It's about the bet."

Hiccup tossed his book to the side, giving Jack his full attention now. They had been waiting for what felt like months for Jack to either win or lose the bet.

Hiccup was the only person he planned on telling. He didn't want Pitch to know and he knew Hiccup could keep his mouth shut if Jack asked him to. Jamie was a different story.

He trusted Hiccup with his life.

"I slept with her last night."

Hiccup smiled and leaned forward, hitting Jack's shoulder "Dude! How was it?"

Jack rolled his eyes. He wasn't about to go into detail about having sex with her, even if it's just Hiccup, it's awkward for him. What could he possibly tell him? That it was nice to actually have sex with a girl he cared about? He chuckled and shook his head "It as okay, seeing as she had never done it before." he shrugged trying to play it off as a big deal.

"Why don't you want to tell Pitch and Jamie?"

Jack looked away from him. This was the part he had trouble deciding "I... Just don't want them to know."

"Jack. There's more to it than just that" Hiccup said with an eye roll.

Jack had almost forgotten who he was talking to. Hiccup Horrendous Haddock III. His best friend for as long as he can remember. The only person who can read him like an open book. It was no surprise when he realized Jack was hiding something.

"I think I fell in love with her"

Hiccup was expecting a secret, but that he fell in love with Rapunzel? He wasn't expecting that. "In love... With Rapunzel Corona?"

Jack gave Hiccup an innocent look "She's better than Elsa"

"_Anyone_ is better than Elsa." Hiccup said with a smile "Does Rapunzel know?"

Jack shook his head. He had wanted to tell her the night before the minute he realized it. Who knew Jackson Overland could get nervous? He had never gotten nervous a day in his life, and then he met Rapunzel.

"I couldn't do it. I was going to when I figured it out, but she made me really nervous?"

Hiccup didn't bother holding back his laughing. He had never heard his best friend get nervous before, so it was funny to him "Rapunzel made you nervous? Little Rapunzel Corona? She's like half your size, dude!"

Jack rolled his eyes and crossed his arms "Not nervous that she would hurt me, nervous that she would reject me?"

"She slept with you, I don't think she would reject you." Hiccup chuckled and shook his head, leaning back to pick his book back up "Now if I fail this test because you're too chicken to tell Rapunzel, I'm hurting you."

Jack rolled his eyes "You're a nerd"

* * *

"We're waiting, Rapunzel." Merida said, with a smile on her face.

Rapunzel turned so her back was now to her friends. She had told them all about her and Jack's date, and how it ended. Ana and Merida seemed excited by it, but Astrid had this look like she wanted to kill him.

"He was sweet and gentle."

Merida and Ana squealed with excitement while Astrid snorted. She swore when she saw Jack she was going to kill him.

"That's so exciting, Punzie!" Ana smiled.

"What's exciting?" Jack asked as he walked over to them.

Rapunzel smiled up at him and kissed his cheek "It's nothing."

Jack looked away from Rapunzel and at her friends. Merida and Ana were both smiling like they were up to something. Then his eyes landed on Astrid who was glaring daggers at him. In the blink of an eye she had stepped forward and punched him in the chest "You're such an idiot, Jack."

Jack's eyes widened and he put a hand up to his chest "You're going to kill me one day, Hofferson."

Astrid rolled her eyes and grabbed Jack's arm, pulling him away from Rapunzel. Rapunzel watched, her eyes wide. She knew Astrid had a low tolerance for the guy, but she didn't know she would hit him over God knows what.

Jack pulled his arm away from Astrid and glared "What was that for?!"

"You slept with her?"

"Yes." He didn't bother hiding it from Astrid. She would hurt him ten times worse if he even tried to lie "Did Hiccup tell you?"

"Rapunzel."

Jack crossed his arms "Sometimes I forget your friends with someone like her."

"I'm going to ignore that comment." she said with a glare "Why haven't you said anything to Pitch?"

"I don't plan to. And I really don't want you to either."

Astrid raised an eyebrow "Why not?"

Jack sighed. Astrid was the last person he wanted to tell about his feelings for Rapunzel, but she was going to find out sooner or later, right?

"I actually like her. And I know that once Pitch finds out that I slept with her he'll try to get me on some other one of his bets, and I don't want to leave Rapunzel."

Astrid's face relaxed and she smiled "You actually like her?" Jack nodded and was expecting to be hit, since that's what Astrid always did when he realized things too late. He was surprised when she pulled him into a hug "Jack! That's so good to hear from you!"

Jack pushed her away with a laugh "If you don't mind, I'm going back over to her. Also, do me a favor, and not tell Jamie."

Astrid tilted her head to the side "What? Why?"

Jack chuckled "Sometimes, he can't keep his mouth shout."

Astrid was going to protest but shut her mouth and nodded instead, he did have a point. She watched him walk back over to Rapunzel, slipping an arm around her waist.

Those two were good together.


	8. Set Up

_**Set Up**_

Rapunzel was laying in the floor, laughing at some joke Jack had just told her. He rolled his eyes at her with a smile "It wasn't that funny, Punz."

Rapunzel sat up and nodded "Yes it was!"

Jack raised an eyebrow at her as she made her way across her room to her phone that was now ringing "It really wasn't." he said with a chuckle.

He leaned back against her bed as she came and sat back down next to him, phone to her ear. Jack could hear the familiar Scottish accent of their now mutual friend, Merida. He had no idea what she was saying but it sounded like she was freaking out over something. Rapunzel sighed "Mer, calm down I'm sure he likes you just fine." she paused then tilted her head to the side "Actually, since when do you freak out over guys?"

Jack got curious and leaned closer so he could hear who she was talking about. Rapunzel gave him a questioning look and he just shrugged but continued trying to hear.

That's when he heard the name he thought he would never hear Merida complaining about. Hiccup.

He couldn't stop himself from laughing. Merida likes Hiccup? He was met with a fist to his arm, and turned to see Rapunzel glaring at him. She moved the phone away from her face "For laughing, you're going to help me set up a date for them"

Jack's smile fell and he shook his head "No, there's no way Hiccup would be interested in her."

Rapunzel smirked "Do you really think that?" he nodded "They've been talking for a few weeks now."

Jack's jaw dropped "I'm going to kill him."

She put the phone back to her face, telling Merida to come to her house later that night, and that she had a surprise for her. Merida only groaned, saying that this had nothing to do with Hiccup, but she'd be there.

Rapunzel sat on her knees, turning to face Jack "Tell Hiccup to come over tonight."

"Punz, is this a good idea?"

"No. It's a great idea!"

She reached towards his hands and he let her take them, confused as to what she was doing. When she sat in his lap is when he got more concerned and tried to push her away "You are aware Flynn is just in the other room and if he comes in right now, he would kill me?"

"I'm fully aware."

"Then what are you doing?" She moved one of her hands and reached for his pocket, causing him to try and back away again "Seriously, Punz, what are you doing?"

She pulled his phone out triumphantly and jumped off his lap, standing up "I was after this. Since you aren't going to tell Hiccup, I will."

Jack stood up and walked behind her, reading what she was typing out to Hiccup, telling him to be at her house at eight. He rolled his eyes as she handed his phone back to him "Now. We have stuff to do"

"Don't you mean _you_ have stuff to do? It's your idea."

Rapunzel turned to him, hands on her hips, and a glare on her face "Hiccup is your best friend, and Merida is mine. She likes Hiccup, and I can tell that he likes her. You want your best friend to be happy, don't you?"

"Of course, but-"

"No buts, Jackson. You're helping whether you like it or not." Jack groaned and Rapunzel's face softened. She held a hand out to him "If you help, there will be something in it for you later."

Jack smiled at her, taking her hand. She led him down to the kitchen "We're going to make them a nice romantic dinner and sit them out on the patio with candles"

Jack laughed and leaned against the counter "Won't your family find this a bit strange?"

Rapunzel started searching through the cabinets for things "My parents love Hiccup and Merida and Flynn is going out with Ana, so it'll just be us and them." her face scrunched up as she opened up another cabinet "What does Hiccup like?"

Jack stared at her for a few seconds, thinking about it. He couldn't think of anything that he didn't like. He would eat anything that was in front of him "He likes everything. I mean, he always eats whatever my family gives him. The only thing he doesn't like is fish, I think."

"That was a dumb question." she said pulling down a box and looking at the back "He's a boy, boys will eat anything. Is he allergic to anything?"

"Mushrooms."

She made a face and put the box back "That's out then." she tapped her chin and looked around the kitchen "I guess spaghetti is romantic enough. It's one of Merida's favorites. But we need a side dish. What's a good side dish to go with Spaghetti?"

"Garlic bread? Salad? I don't know, you're the cook here."

"Or both! Jack, you're a genius!" she pulled him into a quick hug before pulling away and going over to the fridge to pull things out for a salad, throwing it at him "You make the salad. I'll make everything else. This is going to be so perfect!"

Jack mumbled something to himself. He didn't know how to make a salad. He never cooked anything in his life "Uhm, Punz, I don't know how to do this."

Rapunzel set the pot of water on the stove and turned to look at him "Do you know how to make spaghetti then?" he shook his head and she sighed "Then you'll just help. Watch the water, and when it starts to boil break these in half and put them in, and then stir it."

Jack nodded in understanding and leaned on the counter next to the stove and watched her. He could tell that she loved cooking just by watching her. She had a smile on her face and was humming to herself "Why are you watching me?" she asked him, without even looking over at him.

Jack just smiled and crossed his arms "You just look beautiful."

Rapunzel stopped what she was doing for a second before she smiled, and Jack swears he could see her blushing. She quickly went back to making the salad to keep herself distracted, causing Jack to chuckle.

"It's like, six thirty. Is all this even going to be done by eight?" Jack asked, looking into the pot to see if it was boiling yet.

Rapunzel set the salad bowl off to the side and looked at him "Should be. If anything, the garlic bread will be the only thing that's not cooked." she walked over to him and slipped her arms around his waist and looking up at him "We are such good friends."

Jack chuckled and wrapped his arms around her, leaning down to kiss her "They're lucky to have friends like us."

"Keep your hands to yourself, Overland." Merida said as she walked into the kitchen, throwing her bag on the table "You didn't tell me he was going to be here."

"I'm always here." he said tightening his hold on Rapunzel.

"Making dinner, Punzie?"

"Yeah! I knew you were upset over the thing, so I decided to make you your favorite. With a salad and some garlic bread."

Merida fell into one of the chairs and picked up an apple "Sounds delicious."

Rapunzel pulled the collar of Jack's shirt so he was down to her level and she whispered something in his ear. He nodded and made his way to the living room, grabbing what she told him to, and then went out back.

"So, Mer," Rapunzel started as she put the noodles in the pot and stirred "this is sort of a... Double date."

Merida raised her eyebrows at her "What do you mean?"

"I mean, after we got off the phone I kind of told Hiccup to come over later." she shrugged and looked down into the pot.

"Punzel! I can't believe you would do that! He's not interested, thats what I was saying! He hasn't shown any sign of interest at all"

The back door shut and Jack leaned against the wall next to it "As his best friend, I know when he's interested in someone. And he hasn't been himself recently, so either he's really into you, or he's dying. Take your pick."

Rapunzel chuckled, knowing that Jack actually had no idea how Hiccup felt. But she did find it nice that he was trying to cheer her best friend up.

"He should be here soon." Rapunzel said turning around and checking the noddles before finally starting the bread "You should go upstairs and wash up."

Jack smirked "Make yourself look good for Hic."

Merida turned and shot him a glare "I won't hesitate to hurt you."

"You won't be hurting him anytime soon. Now go" Rapunzel said, rolling her eyes at the two.

xxxxxxxxxxx

"Why did you want me to come over here?" Hiccup asked as Jack pulled him into Rapunzel's house.

"It's Rapunzel's idea. I've learned not to question her actions." before Hiccup could say anything Jack punched his arm "Why didn't you tell me you were interested in the redhead?!"

Hiccup rubbed his arm and glared "Stop hanging around Astrid. I didn't want to tell you in case it didn't work out, which I'm pretty sure it's not."

Jack smiled and shrugged "You never know, Hic." he walked towards the kitchen and Hiccup followed, confused by what he meant.

"Hiccup! You're here!" Rapunzel said with a smile while holding a plate of spaghetti "Jack, take him out back. I'll be right there."

Jack nodded and motioned for Hiccup to follow him "What's going on?"

"You'll see."

Jack pulled the back door open and pulled Hiccup outside. Sitting at the table that was set up was Merida. Hiccup's eyes widened and he looked at Jack who pushed him towards the table and went back inside.

Rapunzel raised her eyebrow at him "What did you do?"

"I pushed him towards the table because he seemed frozen in his spot, and then I came back in."

Rapunzel rolled her eyes and shoved a plate towards him "Take this out to Merida. I'll bring Hiccup's"

Jack sighed but nodded, heading to the backyard. Merida and Hiccup looked so awkward, just sitting there either staring at the ground or the sky. Jack rolled his eyes, he knew Hiccup was better than this. He set Merida's plate in front of her and when he walked back Hiccup, punched him in the shoulder and whispered "Talk to her!"

Rapunzel walked out as he was walking back in. She had a smile on her face and was holding a plate in one hand and something else in her other. Jack watched through the window as she made small chat with them and then lit some candles before coming back inside.

She walked up behind Jack and opened the window just enough so they would be able to hear "They're going to get together after tonight."

Jack studied Hiccup's face and how nervous he was before nodding "I've never seen Hiccup so nervous."

"And Merida has never complained about a boy before."

Jack slipped an arm around her waist as they watched their two best friends. Jack looked down at her "I'd have to say this is the nicest thing I've done for any of my friends."

"Well Hiccup is lucky to have a friend like you then."

Rapunzel looked up when she heard Merida say she wanted to get to know him. Jack quieted down and raised an eyebrow. They've been talking for weeks according to Rapunzel, and they didn't know each other?

"Ask anything you want."

The couple that was outside got quiet while Merida thought of what she wanted to ask, and when she finally did, it took Hiccup off guard a little.

"Who was your first kiss?"

Hiccup glanced at the window. He knew Jack and Rapunzel were standing there, and he also knew that Jack had no idea who his first kiss was. Hiccup sighed and messed with his fork before answering "Rapunzel."

Jack's eyes widened and he looked down at her "You were his first kiss?!"

"And he was mine." she was leaning closer to the window to listen. Merida seemed just as shocked as Jack was. She could feel his eyes on her so she leaned away and looked up at him "Are you jealous?"

"No. I have no reason to be jealous, I can kiss you now."

"You're jealous."

"I'm not."

"I can see it in your eyes. You are"

Jack shook his head and pulled her closer, leaning down "Can I tell you something?" she nodded and he took a deep breath "I love you, Rapunzel."

Rapunzel smiled and pulled his face closer to hers "I love you too."

Jack closed the gap between them before pulling away "I need to go make a call real quick. Keep an eye on them."

Rapunzel nodded, not concerned at all and she leaned towards the window again to watch.

Jack was up in Rapunzel's room, picking his phone up off her bed. He knew what he had to do, and he was more than happy to do it. He put the phone up to his ear and listened as it rang, fingers crossed that the person would answer.

"Hello?"

Jack got nervous when he heard the voice. It sent chills down his spine, and made him want to change his mind. He took a deep breath before he started talking "Pitch? I want to call off the bet."


	9. Secrets Revealed

_**Secrets Revealed **_

"Jack, I can't believe you! How could you do something like that?!"

Jack watched Rapunzel pace around the bleachers. She had practically dragged him out here and he has no idea why, or what he did to cause her to yell at him.

"What are you talking about, Rapunzel? What did I do?"

Rapunzel stopped in front of him, a glare on her face "Was I just a bet to you? To see how many times you could sleep with me?"

Jack's eyes widened. They had gone over this when Elsa had talked to her, and now again?

"I wouldn't do that to you, Punz."

He reached out to take her hands in his but she jerked them away "Then why did one of your friends tell me that I was nothing but a bet to you? That you don't really care, that _everything_ was fake?" She shook her head, the tears now falling "I trusted you, Jack, and you were just using me to win some bet"

Jack stood up, looking down at her "You weren't just some bet to me. _I love you_, Rapunzel, whether you want to believe it or not. Making the bet, it was one of the stupidest things I've ever done. And I swear to you, I called it off once I got to know you. Once I realized you're worth more than some dumb bet."

Rapunzel made eye contact with him for the first time since she brought him out there "So it's true then? You really did make the bet?"

Jack wanted nothing more than to just leave, he knew there was no fixing things now. She knew, this was the end. The end of the best relationship he ever had. He couldn't stand looking into her eyes anymore. They were filled with heartbreak and disappointment, and he hated it.

"I'm sorry, Rapunzel. It started out as some bet but I ended it because I didn't want to hurt you. I didn't want you to find out about it at all. I care about you, nothing in the relationship was fake."

Rapunzel laughed. It wasnt like her usual laugh, the one that brought a smile to his face. It was bitter. Her arms were crossed and she was looking away from him "What we had wasn't a relationship. The whole thing was fake, it was based on a bet! I thought you were better than Pitch, it's why I gave you a chance. And it was a mistake."

Before Jack could say anything else, Rapunzel had gathered herself and was heading back towards the school.

Jack shook his head, he couldn't just let her go like that. He ran off the bleachers, following her "Rapunzel! Rapunzel, wait!" She pulled the doors to the school open, Jack still right behind her. He kept calling her name, but she was ignoring him.

He stopped once he was in the school, he had someone else he needed to find. He looked around the hall before walking to where Hiccup and Jamie were, hoping that Pitch was there too.

"Where's Pitch?"

Hiccup and Jamie looked over at him. They both shrugged and Jamie walked over to him "Are you okay, dude? You look terrible."

"I need to find Pitch."

"What'd he do?" Hiccup asked, raising an eyebrow.

Jack looked over at him "He told Rapunzel about the bet."

Hiccup gave Jack a confused look. He remembered talking to him after the date him and Rapunzel had set up, and he remembered Jack saying that he told Pitch he wanted to call off the bet. Hiccup pushed himself off the wall and stood in front of Jack "Why would he do that? I thought you called it off."

"I did. But I guess he didn't like it so he told her."

"That's... That's low, even for Pitch." Jamie said, shaking his head.

"I need to find him"

Hiccup sighed "What are you going to do when you do find him? You aren't one to fight."

Jack shrugged, opening his mouth to say something. Before he could get any words out he was shoved into the wall. He was going to yell at whoever it was until he saw the face. The face of a pissed off Astrid Hofferson. "What the hell are you doing?!"

Astrid was shooting daggers at him. Jack could see it in her eyes that she wanted to kill him. He looked down at her hands that were now forming fist "Rapunzel won't talk to me because she's convinced I knew about that stupid bet!"

"You did, though." Jamie said quietly from behind her.

Astrid closed her eyes before slowly turning to face Jamie, pointing a finger at him "If you don't keep your mouth shut, I'll hurt you next."

Hiccup threw a hand over his mouth so neither of them would see him laughing. He quickly turned away when both Jamie and Jack shot him a look.

Astrid turned back to Jack and brought one of her fist up, wanting nothing more than to hit him, but instead punching the wall next to him "Are you aware of what you did? She was one of my closest friends, you better fix this, Jack, you and I both know I won't hesitate to beat you."

She pulled her arm back again but before she could either hit him or the wall, Jamie was pulling her away "You let me go, Jamie Bennett! He needs to be taught a lesson!"

Hiccup stood in front of Jack, now facing Astrid "Jack called off the bet, Pitch didn't take it very well so he told Rapunzel about it. She, I guess, ended things with Jack, and because you're his friend, I think she's just assuming things now."

Astrid got out of Jamie's hold and pushed Hiccup out of her way "Did you really call the bet off?"

Jack nodded "I had to. I told you how I felt about her, keeping the bet going would have been dumb."

Astrid nodded, not taking her eyes off Jack "You need to fix things with her."

"I know this, Astrid. Do me a favor though, if you see Pitch, take your anger out on him. Okay?"

Astrid smirked and crossed her arms "I've got you."

* * *

"Elsa, right?"

Rapunzel had been looking for Elsa all throughout lunch. She finally saw her walk in with some girl, but she needed to talk to her. She was standing behind Elsa, her books hugged to her chest.

Elsa turned to look at her, a little surprised that Rapunzel had been looking for her "Yeah," she nodded "do you need something?"

Rapunzel glanced around the table "Actually, can I talk to you? Alone?"

Elsa nodded again and turned to Anna, telling her that she'd be right back. Rapunzel led her out into the hall and looked around, making sure there was no sign of Jack "What do you need to talk about?"

"Jack."

Elsa's eyebrows raised and she leaned against the wall "What'd he do?"

Rapunzel let out a shaky breath and looked at the ground "Um, well, I should have listened to you when you tried to warn me about him and the bet."

Elsa tried to read her face but she was staring at the ground. She actually felt kind of bad for her. Rapunzel was known as one of the sweetest girls around their school "How'd you find out?"

"One of his friends, Pitch, he came up to me this morning and told me all about the bet and how he didn't care and that he was probably just going to end things soon."

Elsa sighed, walking towards Rapunzel and putting her hands on her shoulders "Let me tell you something about Pitch, he's a douche. Jack doesn't like him at all. I know the bet was real, but after I talked to you that one day, Jack came and talked to me. He said he cared about you, and I could tell he wasn't lying."

"But... You're the one who told me he was bad news."

Elsa nodded "I know, so I'm contradicting myself here. But there ways to tell if Jackson Overland likes someone, and openly admitting that he cares about whoever it is."

Rapunzel bit her lip "What other ways are there?"

Elsa smiled and took a step back "Did you ever meet Emma?" Rapunzel nodded "If you don't have Emma's approval, he'd still be with you. Which means a lot, because Emma and her approval mean the world to him."

Rapunzel thought about it before laughing a little "I think Emma liked me though."

"He hates spending his money on other people."

Rapunzel folded her arms "He bought me things all the time."

Elsa made Rapunzel look up at her and she gave her a smile "Everyone can tell that Jack likes you. You'd have to be blind not to notice it. And him making that bet was really stupid, but you should really talk to him. It could either end things between you guys for good, or fix things."

Rapunzel nodded slowly. She was in no mood to talk to Jack now, but she knew Elsa was right. It's just the matter of _when_ she would talk to him.


	10. Forgive and Forget

**_Whaaaat, it's the last chapter? _**

**_I want to thank everyone who favored, reviewed, and followed this story! I love you all, okay (:_**

**_Wow, I'm such a slacker. I'm so sorry this took so long! _**

**_Forgive and Forget_**

Jack was sitting on the couch next to Emma, his head leaning against the back of it and he was staring up at the ceiling. Emma was watching him out of the corner of her eyes and sighed. She may be fourteen, but she wasn't stupid. She knew when her brother was upset, and he had been moping around for days. She sat up straight and reached over, shoving his arm "Stop moping around, Jackson."

He looked over at her and raised an eyebrow "I'm not moping. I'm sitting."

"But you're upset."

"Yes." He said with a nod "But I'm not moping."

Emma crossed her arms and glared at him. She'd met all of his girlfriends and she only approved of a few, Rapunzel being one of them. She wanted to see more of Rapunzel around, but she was guessing by the way Jack was acting that it wasn't going to happen "Why hasn't Rapunzel been around?"

Jack sighed and looked over at her "Something stupid happened, we aren't together anymore."

"What did you do?!"

"Why do you automatically assume _I_ did something wrong?"

Emma looked over towards the doorway when Hiccup walked in with Astrid. Emma had only met Astrid a few times, but she could tell by her face that she wasn't happy.

"Because you're Jack, you always do something wrong."

Jack looked over at Astrid when she started talking and frowned "Thanks, Astrid. Why are you here?"

Astrid walked over to the couch and sat herself in between Jack and Emma and turned herself so she was facing Jack "Rapunzel." Jack groaned and leaned back into the couch. If there was one thing he was tired of, it was hearing Rapunzel's name. "You need to talk to her, Jack."

Hiccup had sat himself in the chair next to the couch and leaned forward, resting his elbows on his knees "According to Flynn, she's got herself locked in her room refusing to talk to anyone." Jack sighed and looked over at him "You're pretty much the only person that can get through to her."

Jack laughed and shook his head "She's not going to talk to me. She' sheen avoiding me. And how are you expecting me to get by Flynn?"

Astrid started saying something to him and Emma looked between the three of them. She sighed, she wished she knew what Jack had even done to her. Sure, she knows her brother is an idiot sometimes, but she really thought he liked her. She stood up and walked towards the door and Jack looked at her, interrupting Astrid "Where are you going?"

"I'm giving you privacy with your friends while you talk a both Rapunzel."

Before he could say anything else, she was out the door. She sighed and made her way to the sidewalk. She wants to help Jack, it's boring when he sits around the house all sad.

She stared up at the house she stopped at and took a deep breath. If Jack wasn't going to fix things with her, or at least talk to her, she'd help. It was part of her job as a sister to keep her brother happy.

She walked up to the door and knocked. She had never met Rapunzel's family before, so she was a little nervous but she would suck it up for the sake of her brother. The door was pulled open and someone she guessed was her brother looked at her "Hi?"

Emma looked down at her hands and then back up at the guy "Is Rapunzel here?"

"Yeah, but she's-"

Emma pushed her way past him and pointed upstairs "Where's her room?"

"Second door on the right."

Flynn watched her walk up the stairs. He had never seen this girl before, but she looked familiar. He shook his head and walked back to the living room, maybe she'd be able to get Rapunzel out of her room.

Emma slowly walked up to the door that she was told was Rapunzel's. She paused for a few seconds, trying to figure out what she was going to say to her. She knocked softly and heard movement before she heard sniffling "Go away, Flynn"

Emma sighed and rolled her eyes "It's not Flynn. It's Emma."

Rapunzel's room fell silent. Emma? As in Jack's sister, Emma? Rapunzel climbed off her bed and slowly made her way towards the door before opening it a crack "Why are you here?"

Emma took in her appearance. Her eyes and nose were red from crying, her hair was a mess and she was in sweatpants and an oversized T-shirt. The few times she had seen Rapunzel she was always dressed up, no matter the day or what her and Jack were doing.

"I want to talk to you about Jack."

Rapunzel glared at her and shook her head "He's the last person I want to talk about."

"Rapunzel, please. It's important."

Rapunzel stared at Emma for a few seconds before opening her door completely and letting her in. She turned to face her after shutting the door and walked back to her bed, picking Pascal up and looking down at him "So, what is it?"

"What happened between you two?" She looked over at Rapunzel who didn't look away from Pascal, and said nothing "I don't know what happened, but you both are obviously upset. He's been moping around for days and from what I've heard you've been locked up in your room. If you both are so miserable without each other, why not fix whatever happened?"

Rapunzel finally looked up at her "What Jack did was unforgivable. I don't even see why _he's _so upset. He has no reason to be."

Emma crossed her arms and glared at her "I know that Jack can be a jerk, trust me. I know. I've seen him with all his girlfriends. I've seen how he acts around them and have noticed the way he looks at them. I thought I saw it all with Elsa, but then you came along."

Rapunzel's face fell at the mention of Elsa's name. Whatever Emma was getting at wasn't making her feel any better "And this helps me... How?"

"He actually loves you, Rapunzel. Him and Elsa dated for months and he never said it to her once. Just the other day he was talking to North about you and how much he loves you and how he had no idea how to even tell you"

"He could have been lying."

"He doesn't tell North things like that unless he's serious." Emma gave her a smile and walked towards her door "Come back to my house with me and talk to him. I know he cares a lot about you, and I know you care about him, so come talk to him."

Rapunzel bit her lip and looked away from her. She wants to talk to Jack, to fix things with him, but she doesn't want to end up fighting. She shrugged and looked back at her "I don't know, Emma."

Emma sighed "_Please_, Rapunzel. You make him happy, and the house has been boring without his tricks."

"Okay." she said, standing up and putting Pascal in his cage "Just give me a minute."

Emma nodded with a smile and waited for Rapunzel outside her door. She pulled her phone out just to keep herself distracted until the door opened and Rapunzel walked out. She had changed into shorts and a different shirt, put her hair up, but decided not to wear makeup. Emma shrugged, she was just trying to make herself look decent for Jack.

Rapunzel followed her down the stairs and peeked her head "I'm going out, Flynn."

Flynn looked over at her and then at Emma. He smiled at her, happy to see her out of her room "Where are you going?"

"To talk to Jack." she motioned to Emma who was waiting at the front door "This is Emma, Jack's sister."

Flynn frowned "Is that a good idea?"

Rapunzel shrugged and opened the front door "Probably not, but I'm going to anyways."

Emma looked at Rapunzel over her shoulder to make sure she was still there. She felt accomplished that she managed to get Rapunzel out of her room, now she just needed her and Jack to talk so they could fix whatever happened and get back together. She needed her brother to be happy.

She walked into her house and could hear Jack talking to someone, most likely Hiccup and Astrid, those two spent most their time here. She walked towards the living room unnoticed and motioned for Rapunzel to go in there.

Rapunzel nodded and slowly stepped forward.

Astrid was the first to notice her, she swung her arm and hit Jack in the chest "What was that for?!" he asked, glaring at her. She rolled her eyes, ignoring his question and pointed towards Rapunzel. He turned his head and his face softened "Rapunzel?"

She looked down at her hands "Hi Jack.. Can I talk to you?"

Hiccup and Astrid looked at each other before jumping out of their seats. Hiccup looked at Jack "We'll give you two some privacy." he then looked at Rapunzel and smiled "It's good to see you again, Punz."

Rapunzel gave him a smile and waited for them to leave before walking over and sitting in the chair near the couch. Jack watched her before leaning forward, opening his mouth to talk to her but she cut him off "Emma came over today and talked to me. She told me that you're pretty much miserable and that upsets her. She convinced me to come talk to you."

Jack hesitated before looking up and making eye contact with her "Do... Are you still mad at me?"

Rapunzel nodded and tore her eyes away from his "I think a part of me will always be mad at you. I want to be able to forgive you and I want to be able to... Fix... This." she said motioning between them.

Jack stood up and moved so he was now sitting next to her "I want to fix this." he looked down at his feet and sighed "What I did to you... It was one of the stupidest things I've ever done. I promise you I called off the bet but Pitch didn't take it well and he obviously wasn't happy about it. I didn't want to hurt you, I never wanted to hurt you."

"Emma said that you never told Elsa that you loved her." She glanced at Jack out of the corner of her eye and saw him nod "Why?"

He shrugged "Because I didn't love her." he looked up at her and gave her a smile "I'm not _that_ bad of a guy to lie to her like that."

"But... You lied to me."

He shook his head and reached over nervously grabbing her hand "I didn't lie to you about anything. I care about you, and I love you. Nothing about our relationship was a lie."

Rapunzel stared at their hands and smiled "I guess... We were both in the wrong. You for the bet, and I.. I overreacted and should have heard you out."

Jack chuckled and shook his head "You didn't overreact. If you had done something like that, I would have reacted the same way."

Rapunzel turned to face him completely, not moving her hand away "Are... Are we going to be okay?"

"I hope so."

Emma was leaning on the well outside of the living room listening to them. Her arms were crossed and she had a smile on her face. She shook her head and peeked in to see if things were okay. The couple was now talking quietly to each other, but Emma really didn't care what it was about, she was just glad to see that smile back on her brothers face.

**_A/N: I suck, I'm so sorry omg. Emma to the rescue though! Thanks again to all who followed/reviewed/favored this and stuck around while I wss busy being a slacker. (:_**


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